4-(Difluoromethyl)benzenemethanol → 4-(Difluoromethyl)benzaldehyde

HRID 1672568Notes

Reaction equation

HRID 1672568 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][CH:13]([F:22])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1>C(Cl)Cl>[F:12][CH:13]([F:22])[C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 574463234-(Difluoromethyl)benzenemethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 117688064-(Difluoromethyl)benzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium chlorochromate (8.22 g, 38.1 mmol) was added slowly to a mixture of Example 38B (4.02 g, 25.4 mmol) and celite filter aid (8.5 g) in CH2Cl2 (125 mL) at ambient temperature. The reaction was allowed to proceed for 30 min, and then filtered. The filtrate was concentrated in vacuo to give a black oil. Flash chromatography (Analogix® Intelliflash 280™; 15% EtOAc/hexanes eluant; SF40-115 g column) yielded 3.68 g (93%) of the title compound as a colorless oil. 1HNMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.08-8.02 (m, 2H), 7.84-7.76 (m, 2H), 7.18 (t, J=55.5, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give a black oil

Sources & evidence

ORD record
ord-6bfcc31382314b48aa96c67e88e75a5b
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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